All meetings (7)
| Date | Tour | Tournament | Round | Surface | Winner | Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
|---|---|---|---|---|---|---|---|---|---|---|
| 2015-03-06 | ATP | Davis Cup WG R1: CAN vs JPN | Round Robin | Hard | Kei Nishikori | 6-3 | 3-6 | 4-6 | 6-2 | 4-6 |
| 2015-01-04 | ATP | Brisbane | Semifinal | Hard | Milos Raonic | 6-74 | 7-64 | 7-64 | ||
| 2014-09-29 | ATP | Tokyo | Final | Hard | Kei Nishikori | 6-75 | 6-4 | 4-6 | ||
| 2014-08-25 | ATP | US Open | Round of 16 | Hard | Kei Nishikori | 6-4 | 6-74 | 7-66 | 5-7 | 4-6 |
| 2014-06-23 | ATP | Wimbledon | Round of 16 | Grass | Milos Raonic | 4-6 | 6-1 | 7-64 | 6-3 | |
| 2014-05-04 | ATP | Madrid Masters | Round of 16 | Clay | Kei Nishikori | 6-75 | 6-75 | |||
| 2012-10-01 | ATP | Tokyo | Final | Hard | Kei Nishikori | 6-75 | 6-3 | 0-6 |